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After the 2005 season the Kickers were relegated to the USL Second Division. Jeffrey opted against re-signing with the Kickers, and instead signed a contract with the Toronto Lynx. Jeffrey made his Lynx debut on 4 June 2006 coming on as a substitute for Damien Pottinger in a match against the Virginia Beach Mariners. Initially he struggled to find his form and had a six-game goal drought. Soon after he would record his first goal on 21 July 2006 in a 1–1 draw against rivals Rochester Rhinos. He became an instant impact when he would score crucial match-winning goals for the Lynx. His was selected to the USL First Division First All-League team three times, as well as being named USL Player of the Week. He concluded the season as the team's leading goal scorer with nine goals. His efforts led the Lynx to a team-record undefeated streak at home to 10 games, and helped the Toronto club reach the finals of the Open Canada Cup in their debut season in the tournament. After the 2006 season the Lynx franchise dropped two divisions down to the USL Premier Development League, thus releasing Jeffrey from his Toronto contract. He signed with the newly expansion Carolina RailHawks as a free agent. Jeffrey's tenure with Carolina was rather a disappointment, where he failed to re-capture his goal scoring legacy which was known throughout his time in the USL First Division. He appeared in fourteen league games for the RailHawks without recording a single goal, which resulted in his being waived from the team.

After a successful experience at the college level he was drafted first overall by the San Francisco Bay Seals, making his professional debut in 2000. Good form led to an international call-up in 2000, after he was signed by Richmond Kickers. It was at Richmond where Jeffrey was able to establish himself as a consistent striker with a proven track record. Receiving several Team of the Week, and Player of the Week selections; as well as leading Richmond to claim their second Conference title. Once the Kickers were relegated, Jeffrey finished off his career with stints in Toronto, and Carolina.

He was the first overall pick in the 2000 A-League Draft by the San Francisco Bay Seals where he recorded 12 goals and 3 assists as a rookie. In 2001, he signed for the Richmond Kickers, where in his first season with the club he led the Kickers in goals and points, scoring 20 goals, and adding 9 assists, and was named Team of the Week twice.He was the Kickers' leading goal scorer again in 2003 with 10 goals, and 9 assists, and 29 points. He was selected two times as an A-League Player of the Week, and he was honoured as the league's Player of the Week after he recorded two goals and an assist in a win and tie against the Charlotte Eagles in June. Following Jeffrey's season he was named to the All A-League Second Team. In 2005, he helped the Kickers reach the USL Championship final where his team lost in a penalty shoot-out to the Seattle Sounders.

He has also earned one cap with the Trinidad and Tobago national team in 2000.

He started playing amateur soccer with Yavapai Junior College in 1997, where he led Yavapai to a National Junior College Athletic Association championship, earning himself first team Junior College All-American honours, and being named Junior College Player of the Year. Later on he would go and play NCAA soccer with Virginia Commonwealth University for two years, being named to the first team All-Colonial Athletic Association team both years. And winning the Virginia State Player of the Year in 1999 and third team NSCAA All-American. He tallied 29 goals and 7 assists in 38 games for the Rams and hold their school record for most goals in a season with 18, a mark that was once held by John Dugan with 17 in 1987.

Kevin Jeffrey (born 10 October 1974 in Trincity, Trinidad and Tobago) is a former professional football (soccer) forward who spent eight season in the USL First Division. On 7 December 2009 he was appointed Director of Football for the North East Stars in the TT Pro League.